Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. China.
Org Lett. 2021 Oct 1;23(19):7359-7363. doi: 10.1021/acs.orglett.1c02513. Epub 2021 Sep 10.
A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C-H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey-Bakshi-Shibata (CBS) reduction of indanone derivatives. The subsequent diastereospecific and regioselective rhodium-catalyzed silylation of the methyl C-H bond led to indane derivatives with quaternary centers. This strategy was further applied in syntheses of (nor)illudalane and botryane sesquiterpenoids.
通过连续的对映选择性还原和 C-H 官能化反应，开发了一种实用的具有季立体中心的对映体富集茚满衍生物的合成方法。通过 CuH 催化的不对称还原或 Corey-Bakshi-Shibata（CBS）还原，可实现对映选择性良好到优秀的对映体富集的茚满酮衍生物。随后，通过铑催化的甲基 C-H 键的立体选择性和区域选择性硅烷化反应，得到具有季立体中心的茚满衍生物。该策略进一步应用于（去）愈创木烷和 botryane 倍半萜的合成。
